Hiring Your First Dedicated Salesperson: When Did You Make the Leap?

I don't have employees yet, but if I were in this position, I'd lean toward promoting from within. Someone who already understands the business and has established relationships with customers brings real value. I'd consider a 90-day trial with clear sales goals and a base salary plus performance incentives. That would give both the employee and the business an opportunity to evaluate whether the role is a good fit.